CA2173494A1 - Process and Antiparasitic Intermediates for Doramectin - Google Patents
Process and Antiparasitic Intermediates for DoramectinInfo
- Publication number
- CA2173494A1 CA2173494A1 CA2173494A CA2173494A CA2173494A1 CA 2173494 A1 CA2173494 A1 CA 2173494A1 CA 2173494 A CA2173494 A CA 2173494A CA 2173494 A CA2173494 A CA 2173494A CA 2173494 A1 CA2173494 A1 CA 2173494A1
- Authority
- CA
- Canada
- Prior art keywords
- intermediates
- doramectin
- antiparasitic
- compound
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Steroid Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Intermediates and a process for preparing doramectin, the compound of formula (1), semisynthetically from by-product in the fermentation which also yields the compound of formula (I). The intermediates prepared by the process of this invention also have utility as antiparasitic agents. The process of this invention utilizes continuous reaction inert gas sparging during the pyrolysis step, resulting in a significant improvement in the overall yield of this conversion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13181293A | 1993-10-05 | 1993-10-05 | |
| US08/131,812 | 1993-10-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2173494A1 true CA2173494A1 (en) | 1995-04-13 |
| CA2173494C CA2173494C (en) | 1999-04-13 |
Family
ID=22451135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002173494A Expired - Fee Related CA2173494C (en) | 1993-10-05 | 1994-09-19 | Process and antiparasitic intermediates for doramectin |
Country Status (42)
| Country | Link |
|---|---|
| US (1) | US5665708A (en) |
| EP (1) | EP0722453B1 (en) |
| JP (1) | JP2761296B2 (en) |
| KR (1) | KR100186946B1 (en) |
| CN (2) | CN1040113C (en) |
| AP (1) | AP499A (en) |
| AT (1) | ATE185571T1 (en) |
| AU (1) | AU680039B2 (en) |
| BG (1) | BG61842B1 (en) |
| BR (1) | BR9407747A (en) |
| CA (1) | CA2173494C (en) |
| CO (1) | CO4290361A1 (en) |
| CZ (1) | CZ287404B6 (en) |
| DE (1) | DE69421190T2 (en) |
| DK (1) | DK0722453T3 (en) |
| DZ (1) | DZ1816A1 (en) |
| EG (1) | EG20802A (en) |
| ES (1) | ES2138090T3 (en) |
| FI (1) | FI944623A (en) |
| GR (1) | GR3032042T3 (en) |
| GT (1) | GT199400065A (en) |
| HR (1) | HRP940642B1 (en) |
| HU (1) | HU219020B (en) |
| IL (1) | IL111075A (en) |
| LV (1) | LV11474B (en) |
| MA (1) | MA23342A1 (en) |
| MY (1) | MY111320A (en) |
| NO (1) | NO305320B1 (en) |
| NZ (1) | NZ271734A (en) |
| OA (1) | OA10577A (en) |
| PE (1) | PE20595A1 (en) |
| PL (1) | PL177039B1 (en) |
| RO (1) | RO115884B1 (en) |
| RU (1) | RU2120943C1 (en) |
| SI (1) | SI9420059A (en) |
| SK (1) | SK45396A3 (en) |
| TW (1) | TW282472B (en) |
| UA (1) | UA45957C2 (en) |
| UY (1) | UY23839A1 (en) |
| WO (1) | WO1995009863A1 (en) |
| YU (1) | YU49171B (en) |
| ZA (1) | ZA947740B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6248579B1 (en) * | 1998-02-13 | 2001-06-19 | Pfizer Inc | Streptomyces avermitilis gene directing the ratio of B2:B1 avermectins |
| NO312056B1 (en) * | 1998-06-09 | 2002-03-11 | Alpharma As Aquatic Animal Hea | Use of preparations for the prevention and treatment of parasites in fish |
| EP2050815B1 (en) * | 2002-02-12 | 2011-10-26 | Pfizer Products Inc. | Streptomyces Avermitilis gene directing the ratio of B2:B1 avermectins |
| CN104418927B (en) * | 2013-08-29 | 2018-03-27 | 重庆乾泰生物医药有限公司 | A kind of isolation and purification method of doractin |
| CN104693254B (en) * | 2013-12-10 | 2018-03-27 | 重庆乾泰生物医药有限公司 | A kind of preparation method of doractin |
| CN107723325B (en) * | 2017-11-28 | 2021-03-30 | 山东齐发药业有限公司 | Fermentation production method of doramectin based on pH control |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201861A (en) * | 1977-10-03 | 1980-05-06 | Merck & Co., Inc. | Acyl derivatives of C-076 compounds |
| US4328335A (en) * | 1979-08-13 | 1982-05-04 | Merck & Co., Inc. | Process for the interconversion of C-076 compounds |
| US4457920A (en) * | 1981-09-03 | 1984-07-03 | Merck & Co., Inc. | 4a-Substituted avermectin compounds |
| ES8800986A1 (en) * | 1985-07-27 | 1987-12-01 | Pfizer | Antiparasitic avermectin and milbemycin derivatives and process for their preparation. |
| IE67373B1 (en) * | 1985-09-13 | 1996-03-20 | American Cyanamid Co | Macrolide antibiotics and their preparation |
| US4886828A (en) * | 1986-09-12 | 1989-12-12 | American Cyanamid Company | Δ22 -derivatives of LL-F28249 compounds |
| IN167980B (en) * | 1987-01-23 | 1991-01-19 | Pfizer | |
| US4806527A (en) * | 1987-03-16 | 1989-02-21 | Merck & Co., Inc. | Avermectin derivatives |
| GB8807280D0 (en) * | 1988-03-26 | 1988-04-27 | Pfizer Ltd | Antiparasitic agents |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| NZ231773A (en) * | 1988-12-23 | 1992-09-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal pharmaceutical compositions thereof |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| US5262400A (en) * | 1991-06-20 | 1993-11-16 | Merck & Co., Inc. | 4α-substituted avermectin derivatives |
| GB9201505D0 (en) * | 1992-01-24 | 1992-03-11 | Pfizer Ltd | Antiparasitic agents |
| GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
| US5162363A (en) * | 1992-03-18 | 1992-11-10 | Merck & Co., Inc. | 23-nor-23-thia avermectin analogs are active anthelmintic agents |
| US5229415A (en) * | 1992-03-24 | 1993-07-20 | Merck & Co., Inc. | Alkylthio alkyl avermectins are active antiparasitic agents |
| US5229416A (en) * | 1992-04-29 | 1993-07-20 | Merck & Co., Inc. | Avermectin difluoro derivatives |
| US5578581A (en) * | 1994-04-26 | 1996-11-26 | Merck & Co., Inc. | Active avermectin analogue |
-
1994
- 1994-09-19 CN CN94193687A patent/CN1040113C/en not_active Expired - Fee Related
- 1994-09-19 SI SI9420059A patent/SI9420059A/en not_active IP Right Cessation
- 1994-09-19 UA UA96041334A patent/UA45957C2/en unknown
- 1994-09-19 PL PL94313781A patent/PL177039B1/en not_active IP Right Cessation
- 1994-09-19 DK DK94925598T patent/DK0722453T3/en active
- 1994-09-19 RU RU96108798A patent/RU2120943C1/en not_active IP Right Cessation
- 1994-09-19 HU HU9600875A patent/HU219020B/en not_active IP Right Cessation
- 1994-09-19 BR BR9407747A patent/BR9407747A/en not_active Application Discontinuation
- 1994-09-19 AU AU75454/94A patent/AU680039B2/en not_active Ceased
- 1994-09-19 JP JP7510708A patent/JP2761296B2/en not_active Expired - Lifetime
- 1994-09-19 RO RO96-00720A patent/RO115884B1/en unknown
- 1994-09-19 ES ES94925598T patent/ES2138090T3/en not_active Expired - Lifetime
- 1994-09-19 NZ NZ271734A patent/NZ271734A/en unknown
- 1994-09-19 CA CA002173494A patent/CA2173494C/en not_active Expired - Fee Related
- 1994-09-19 US US08/617,740 patent/US5665708A/en not_active Expired - Fee Related
- 1994-09-19 AT AT94925598T patent/ATE185571T1/en not_active IP Right Cessation
- 1994-09-19 CZ CZ1996963A patent/CZ287404B6/en not_active IP Right Cessation
- 1994-09-19 SK SK453-96A patent/SK45396A3/en unknown
- 1994-09-19 DE DE69421190T patent/DE69421190T2/en not_active Expired - Fee Related
- 1994-09-19 WO PCT/IB1994/000283 patent/WO1995009863A1/en not_active Application Discontinuation
- 1994-09-19 KR KR1019960701764A patent/KR100186946B1/en not_active IP Right Cessation
- 1994-09-19 EP EP94925598A patent/EP0722453B1/en not_active Expired - Lifetime
- 1994-09-21 TW TW083108681A patent/TW282472B/zh active
- 1994-09-28 GT GT199400065A patent/GT199400065A/en unknown
- 1994-09-29 AP APAP/P/1994/000678A patent/AP499A/en active
- 1994-09-29 IL IL11107594A patent/IL111075A/en not_active IP Right Cessation
- 1994-09-29 CO CO94044428A patent/CO4290361A1/en unknown
- 1994-10-03 EG EG61394A patent/EG20802A/en active
- 1994-10-03 PE PE1994252070A patent/PE20595A1/en not_active Application Discontinuation
- 1994-10-03 MY MYPI94002615A patent/MY111320A/en unknown
- 1994-10-04 DZ DZ940106A patent/DZ1816A1/en active
- 1994-10-04 HR HR940642A patent/HRP940642B1/en not_active IP Right Cessation
- 1994-10-04 FI FI944623A patent/FI944623A/en unknown
- 1994-10-04 ZA ZA947740A patent/ZA947740B/en unknown
- 1994-10-04 YU YU57294A patent/YU49171B/en unknown
- 1994-10-04 MA MA23664A patent/MA23342A1/en unknown
- 1994-10-05 UY UY23839A patent/UY23839A1/en not_active IP Right Cessation
-
1996
- 1996-04-02 BG BG100470A patent/BG61842B1/en unknown
- 1996-04-03 NO NO961380A patent/NO305320B1/en unknown
- 1996-04-04 OA OA60811A patent/OA10577A/en unknown
- 1996-04-08 LV LVP-96-96A patent/LV11474B/en unknown
-
1998
- 1998-01-09 CN CN98103956A patent/CN1060483C/en not_active Expired - Fee Related
-
1999
- 1999-12-02 GR GR990403129T patent/GR3032042T3/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |